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1-Methyl octanedioate

1-Methyl octanedioate structure

CAS No:
3946-32-5
Formula:
C9H16O4
Chemical Name:
1-Methyl octanedioate
Synonyms:
Octanedioic acid,1-methyl ester;Suberic acid,monomethyl ester;Octanedioic acid,monomethyl ester;Suberic acid,methyl ester;1-Methyl octanedioate;Monomethyl suberate;Methyl 7-carboxyheptanoate;Methyl 1,8-octanedionate;8-Methoxy-8-oxooctanoic acid
Categories:
Pharmaceutical Intermediates > Antineoplastics

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Description

colorless low melting solid

1-Methyl octanedioate Basic Attributes

Molecular Weight：

188.22

Exact Mass：

188.22

DSSTox ID：

DTXSID90339174

HScode：

2918990090

Characteristics

PSA：

63.6

XLogP3：

1.8

Density：

1.047 g/cm³ @ Temp: 20 °C

Melting Point：

17-19 °C

Boiling Point：

146-150 °C @ Press: 1 Torr

Flash Point：

113ºC

Refractive Index：

1.444

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38

safety instructions：

26-37/39

Marks：

Xi: Irritant;

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

1-Methyl octanedioate Use and Manufacturing

Methods of Manufacturing

General procedure: 5.1.2 A mixture of compound 12 (82 g, 0.4 mol), KOH (22.4 g, 0.4 mol) and methanol (450 mL) was stirred at room temperature for 4 h. The solvent was removed under reduced pressure and the residue was taken up with water (200 mL) and washed with ethyl ether (100 mL). The pH of the aqueous phase adjusted to 3 with 10percent HCl, extracted with ethyl ether (3 200 mL). The combined organic phase was washed with brine (100 mL), dried with MgSO4 and concentrated under reduced pressure to afford 13 (31 g, 41percent) as colorless oil. 1H NMR (300 MHz, CDCl3) d: 1.25–1.44 (m, 4H, –CH2), 1.56–1.72 (m, 4H, –CH2), 2.27–2.41 (m, 4H, 2CH2CO2), 3.67 (s, 3H, CO2CH3).General procedure: A solution of KOH (5.87 g, 104.65 mmol) in MeOH (150 ml) was added to dimethyl glutarate (13.15 g, 90 mmol), and the mixture was stirred for 4 h at rt. The solvent was then removed, and Et Saponification of dimethyl suberate to yield suberic acid To a 250 mL round bottom flask equipped with a stir bar, heating mantle, temperature probe, and short path distillation head was added crude dimethyl suberate (1.15 g), Amberlyst 35 (0.2 g, pre-washed with methanol), acetic acid (10 mL), and DI water (2 mL). The reaction was heated to 95 °C for 20 hours with a gentle stream of nitrogen (0.05 SCFH) passing through the headspace. GC analysis showed high conversion of dimethyl suberate to suberic acid as shown in Table 6.Table 6 - GC analysis of crude reaction mixture[0093] The product solution was cooled and filtered to remove catalyst using a syringe filter (0.45 u, polypropylene). The clear product solution was loaded to a 250 mL round bottom flask equipped with a stir bar, heating mantle, temperature probe, and short path distillation head. The acetic acid was distilled out under atmospheric pressure to leave an oily residue. To the residue was added DI water (10 mL). The water was distilled out to leave about 4 mL of solution which was allowed to gradually cool to room temperature with the stirring off. Upon cooling, white crystals were evident. The solid was isolated by filtration and washed with DI water (4 mL). The solids were dried at 100 °C to yield 0.41 g of white crystalline product. A sample of the product was dissolved in acetone for GC analysis and results are shown in Table 7.The solution of compound 9 (2.0 g, 12.8 mmol) in methanol (6.5 ml) was stirred at reflux in pressure tube during 3 h. The reaction mixture was evaporated to dryness and treated with ether. The white precipitate formed was filtered off. Yield 1.92 g(80percent). 1H NMR spectrum (400 MHz, DMSO-d6), δ, ppm(J, Hz): 1.15–1.28 (4H, m, (CH2)2(CH2)2CO2CH3); 1.37–1.52 (4H, m, HO2C(CH2CH2CH2)2CO2CH3); 2.14 (2H, t, J = 7.4, CH2CO2CH3); 2.24 (2H, t, J = 7.4, CH2CO2H);3.54 (3H, s, CO2CH3, partially overlapped with water signal); 11.94 (1H, br. s, CO2H).

Uses

Suberic acid monomethyl ester was used in the synthetic preparation of Prostaglandin E1 (P838600), a primary prostaglandin and a peripheral vasodilator.

Computed Properties

Molecular Weight:188.22
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:8
Exact Mass:188.10485899
Monoisotopic Mass:188.10485899
Topological Polar Surface Area:63.6
Heavy Atom Count:13
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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